Crystal structure and Hirshfeld surface analysis of N-[2-(5-methylfuran-2-yl)phenyl]-3-nitro-N-[(3-nitrophenyl)sulfonyl]benzenesulfonamide

In the crystal, C—H⋯O hydrogen bonds link adjacent molecules in the three-dimensional network, while π–π stacking interactions, with centroid–centroid distances of 3.8745 (9) Å, propagate into chains parallel to the a axis.


Chemical context
The synthesis of sulfonamides has been given considerable attention in the literature. A large number of reports are based on various chemical and physical properties, methods of synthesis and application of sulfonamides (Safavora et al., 2019). The electronic and structural properties of the sulfonamide moiety make it a bioisostere of such compounds as urea, thiourea, carbamates and sulfamides (Reitz et al., 2009;Abdelhamid et al., 2011;Khalilov et al., 2021). Linear and cyclic compounds containing sulfonamide fragments have a wide range of biological activity -they possess antibacterial properties (Yun et al., 2012;Nadirova et al., 2021), show diuretic activity (Logemann et al., 1959;DeStevens et al., 1959), are active against seizures (Thiry et al., 2008) and inhibit various enzymes like human leukocyte elastase and cathepsin G, a HIV-1 protease (Supuran et al., 2003). Sulfonamides are also used as fungicidal (Chohan et al., 2006(Chohan et al., , 2010 and insecticidal mixtures. The most widely used furan-substituted sulfonylamide is Furosemide, a loop diuretic medication used to treat fluid build-up due to heart failure, kidney disease or liver scarring. Typically, furan-substituted monosulfamides are obtained by treatment of the amines with the corresponding sulfonyl chlorides (Pilipenko et al., 2012;Butin et al., 2006;Naghiyev et al., 2020). It turned out unexpectedly that the interaction of 2-(-furyl)aniline with sulfochloride containing the electron-withdrawing 3-nitrophenyl group under the same conditions gives a double sulfarylation product (Fig. 1), which is possible only with the use of strong bases (Bartsch et al., 1977;Li et al., 2022). The obtained product can serve as a compound for studying furan fragment-opening (Pilipenko et al., 2012;Butin et al., 2006) or the Diels-Alder reactions of furans (Borisova et al., 2018a,b;Krishna et al., 2022;Zubkov et al., 2007) and for studying biological activity. On the other hand, intermolecular noncovalent interactions organize the molecular aggregates, catalytic intermediates, etc., which play a critical role in the functional properties of heterocyclic compounds (Gurbanov et al., 2020a(Gurbanov et al., ,b, 2022Ma et al., 2021;Mahmoudi, et al., 2017a,b;Mahmudov et al., 2011Mahmudov et al., , 2022.

Structural commentary
In the title compound (Fig. 2), the angle between the planes of the arene rings (C12-C17 and C18-C23) of the (3-nitrophenyl)sulfonyl groups are 40.87 (7) . The furan ring (O1/C7-C10) is inclined at angles of 51.04 (8) and 12.78 (8) with respect to the arene rings (C12-C17 and C18-C23) of the (3-nitrophenyl)sulfonyl groups, while it makes a dihedral angle of 20.77 (8) with the plane of the arene ring (C1-C6) attached to the furan ring. The arene ring attached to the furan ring makes dihedral angles of 33.19 (7) and 17.84 (7) , respectively, with the arene rings of the 3-nitrophenyl)sulfonyl groups. The geometric properties of the title compound are normal and consistent with those of related compounds listed in the Database survey (Section 4).

Figure 2
The molecular structure of the title compound, showing the atom labelling and with displacement ellipsoids drawn at the 50% probability level.

Database survey
The nine related compounds found as a result of the search for 'N-(methanesulfonyl)-N-methyl methanesulfonamide' in the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016) (Li & Song, 2008).
In JOBTIF (space group P2 1 /n), molecules are linked by pairs of C-HÁ Á ÁO hydrogen bonds, forming inversion dimers. In CEGMIM (space group Pbca), molecules are connected by C-HÁ Á ÁO interactions into sheets in the ab plane. In YAXKAL (space group P1), molecules associate via pairs of N-HÁ Á ÁN hydrogen bonds, forming a centrosymmetric eight-   The crystal packing along the a axis, showing the C-HÁ Á ÁO hydrogenbond network and thestacking interactions.

Figure 4
The crystal packing diagram along the b axis, showing the intermolecular C-HÁ Á ÁO hydrogen bonds. membered {Á Á ÁHNCN} 2 synthon. The crystal structure of OCABUR (space group P2 1 /c) is stabilized by intermolecular C-HÁ Á ÁO hydrogen bonds. In the crystal of CEGSUE (space group P1), the only possible directional interactions are very weak C-HÁ Á Á interactions and very weakstacking between parallel methylphenyl rings. In EFASUB (space group C2/c), molecules associate via N-HÁ Á ÁN and N-HÁ Á ÁO hydrogen bonds, forming extended hydrogen-bonded sheets that lie parallel to the bc plane. The N-HÁ Á ÁN hydrogen bonds propagate along the b-axis direction, while the N-HÁ Á ÁO hydrogen bonds propagate along the c-axis direction. In the crystal packing of PONZIC (space group P1), molecules are linked into chains parallel to the a axis by intermolecular C-HÁ Á ÁO hydrogen bonds andstacking interactions. In the crystal structure of AYUPUG (space group P2 1 /c), weak C-HÁ Á ÁO interactions connect the molecules in a zigzag manner along the a axis. In ROGJON (space group Pbca), the crystal sructure exhibits weak intermolecular N-HÁ Á ÁO, C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds and interactions.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3    riding contributions with isotropic displacement parameters fixed at 1.2U eq (C) (1.5 for the methyl groups).

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.